US3215686A - Monoazo dyestuffs - Google Patents
Monoazo dyestuffs Download PDFInfo
- Publication number
- US3215686A US3215686A US252605A US25260563A US3215686A US 3215686 A US3215686 A US 3215686A US 252605 A US252605 A US 252605A US 25260563 A US25260563 A US 25260563A US 3215686 A US3215686 A US 3215686A
- Authority
- US
- United States
- Prior art keywords
- yellow
- group
- pyrazolone
- methyl
- monoazo dyestuffs
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 title description 7
- 230000008878 coupling Effects 0.000 description 6
- 238000010168 coupling process Methods 0.000 description 6
- 238000005859 coupling reaction Methods 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- -1 aminoazo Chemical group 0.000 description 5
- 238000004043 dyeing Methods 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 238000007639 printing Methods 0.000 description 3
- NHLAPJMCARJFOG-UHFFFAOYSA-N 3-methyl-1,4-dihydropyrazol-5-one Chemical compound CC1=NNC(=O)C1 NHLAPJMCARJFOG-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical class C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 150000008049 diazo compounds Chemical class 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- XJCVRTZCHMZPBD-UHFFFAOYSA-N 3-nitroaniline Chemical compound NC1=CC=CC([N+]([O-])=O)=C1 XJCVRTZCHMZPBD-UHFFFAOYSA-N 0.000 description 1
- CWJQQASJVVAXKL-UHFFFAOYSA-N 4-(3-Methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl)benzenesulfonic acid Chemical compound O=C1CC(C)=NN1C1=CC=C(S(O)(=O)=O)C=C1 CWJQQASJVVAXKL-UHFFFAOYSA-N 0.000 description 1
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- AMXBISSOONGENB-UHFFFAOYSA-N acetylene;ethene Chemical group C=C.C#C AMXBISSOONGENB-UHFFFAOYSA-N 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- PEMGGJDINLGTON-UHFFFAOYSA-N n-(3-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=CC(N)=C1 PEMGGJDINLGTON-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000004552 water soluble powder Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
- C09B62/78—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring with other reactive groups
- C09B62/82—Azo dyes
- C09B62/825—Monoazo dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
- C09B62/465—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being an acryloyl group, a quaternised or non-quaternised aminoalkyl carbonyl group or a (—N)n—CO—A—O—X or (—N)n—CO—A—Hal group, wherein A is an alkylene or alkylidene group, X is hydrogen or an acyl radical of an organic or inorganic acid, Hal is a halogen atom, and n is 0 or 1
- C09B62/47—Azo dyes
- C09B62/473—Monoazo dyes
Definitions
- Z is a bivalent radical of the group consisting of S0 SO, 0 and S,
- R is a substituent of the group consisting of a hydrogen atom and the radical R, R is a radical of the group consisting of alkyl, aryl, aralkyl and cycloalkyl, R" is a substituent of the group consisting of OH and R' is a substituent of the group consisting of a hydrogen atom, alkyl and aryl, R" is a radical of the group consisting of methyl, phenyl, carboxyl, carbamido and carbalkoxy, and n is an integer consisting of 0 and 1.
- the new monoazo dyestuffs may be obtained by known coupling or acylating procedures, namely by coupling ,diazo compounds of arninophenylacylamines which may be further substituted in the phenyl residue and wherein the acylamino residue corresponds to the formula -.-IiI-.XY z
- the dyestuffs may be used for the'dyeing of animal, vegetable and synthetic fibers; they particularly distinguish themselves by yielding, when dyed or printed on cellulose fibers, dyeings and printings which are fast to washing, whereby they react in the form of their solutions or suspensions with these fibers in the presence of alkaline active agents especially at an elevated temperature or by dry heating.
- the dyestulfs are resistant to alkaline active agents, and on the other hand, they may be fixed on the fiber with a good yield so that full dyeings and printings are obtained having very good wet fastness properties and a very good fastness to light.
- Example 1 38.4 kg. 3-(fl-phenylsulfonylpropionylamino)-1-aminobenzene-6-sulfonic acid in the form of its sodium salt are dissolved in water, admixed with 6.9 kg. sodium nitrite and diazotized at 15-20 by allowing the mixture to run into ice and hydrochloric acid. The diazo suspension obtained is combined, in the presence of excess sodium acetate, With an aqueous suspension of about 10.3 kg. 3- methyl-S-pyrazolone. The dyestutf precipitated is filtered off and dried.
- the before-mentioned dyestuffs may also be prepared by starting from the monoazo dyestulfs obtained by combining the diazo compounds of 3-nitro-1-aminobenzene or 3-acetylamino-l-aminobenzene with 1-(4-sulfophenyl)- 3-methyl-5-pyrazolone, by converting these monoazo dyestuffs by reduction or saponification into the aminoazo dyestulf and by acylating the latter in the presence of sodium bicarbonate with the chloride or anhydride of the IS-methylsulfonyl-propionic acid.
- Dlazo component Coupling component Shade 3-methyl-5-pyrazolone Greenish yellow.
- Nmooemomsomom 1 (2,5 diehloro 4' sulfophenyl) B-methylfi-pyrazolone.
- Diazo component Coupling component Shade 1(4-su1fophenyl)-pyrazolone-3-carboxylic acid. Reddish yellow.
- Y is a radical selected from the group consisting of ethylene and vinylene
- Z is a bivalent radical selected from the group consisting of S0 SO, and S,
- R is a radical selected from the group consisting of lower alkyl, phenyl, and benzyl,
- R" is a substituent selected from the group consisting of OH and H2,
- R' is a substituent selected from the group consisting of hydrogen and phenyl
- R" is a radical selected from the group consisting of methyl, phenyl, carboxyl, carbamido, and lower carbalkoxy,
- 50 n is an integer consisting of 0 and 1.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
United States Patent 3,215,686 MONOAZO DYESTUFFS Werner Zerweck and Richard Fleischhauer, Frankfurt am Main, and Heinz Bender, Bergen-Enkheim, Ifieis Hanan, Germany, assignors to Cassella Farbwerke Mainkur Aktiengesellschaft, Frankfurt am Main, e h m, Germany, a company f erm y No Drawing. Filed Jan. 21, 1963, Ser. No. 252,605 Claims priority, applicatigilGolermany, Jan. 22, 1962,
Q 1 Claim. (Cl. 260-162) This invention relates to new and valuable yellow monoazo dyestuffs having the formula in which X is a bivalent radical of the group consisting of S0 and Y is a radical of the group consisting of ethylene vinylene,
Z is a bivalent radical of the group consisting of S0 SO, 0 and S,
R is a substituent of the group consisting of a hydrogen atom and the radical R, R is a radical of the group consisting of alkyl, aryl, aralkyl and cycloalkyl, R" is a substituent of the group consisting of OH and R' is a substituent of the group consisting of a hydrogen atom, alkyl and aryl, R" is a radical of the group consisting of methyl, phenyl, carboxyl, carbamido and carbalkoxy, and n is an integer consisting of 0 and 1.
and
The new monoazo dyestuffs may be obtained by known coupling or acylating procedures, namely by coupling ,diazo compounds of arninophenylacylamines which may be further substituted in the phenyl residue and wherein the acylamino residue corresponds to the formula -.-IiI-.XY z
with pyrazols of the formula H. C C RIIII H II f F wherein X, Y, Z, R, R, R", R and R" have the fore- 3,215,686 Patented Nov. 2, 1965 "ice going meaning, or by acylating monoazo dyestuffs containing free amino groups instead of acylated amino groups with halides or anhydrides of organic acids containing the residue XYZR and by selecting the components in such a manner that the resultant dyestuffs contain not more than one sulfonic acid group.
The dyestuffs may be used for the'dyeing of animal, vegetable and synthetic fibers; they particularly distinguish themselves by yielding, when dyed or printed on cellulose fibers, dyeings and printings which are fast to washing, whereby they react in the form of their solutions or suspensions with these fibers in the presence of alkaline active agents especially at an elevated temperature or by dry heating.
On the one hand, the dyestulfs are resistant to alkaline active agents, and on the other hand, they may be fixed on the fiber with a good yield so that full dyeings and printings are obtained having very good wet fastness properties and a very good fastness to light.
The following examples are given for the purpose of illustrating the present invention. Where not otherwise stated, the temperatures given are in degrees centigrade.
Example 1 38.4 kg. 3-(fl-phenylsulfonylpropionylamino)-1-aminobenzene-6-sulfonic acid in the form of its sodium salt are dissolved in water, admixed with 6.9 kg. sodium nitrite and diazotized at 15-20 by allowing the mixture to run into ice and hydrochloric acid. The diazo suspension obtained is combined, in the presence of excess sodium acetate, With an aqueous suspension of about 10.3 kg. 3- methyl-S-pyrazolone. The dyestutf precipitated is filtered off and dried. It represents a yellow powder and it yelds on cotton, when printed in the presence of sodium carbonate, urea and alginate thickening and subsequently dried, steamed, rinsed and soaped, greenish yellow printings of a very good fastness to washing and light. The good fastness to light is retained even after crease-proof finishing.
E ample 2 24.2 kg. 1-amino-'3-( fl-methylsulfonylpropionylamino)- benzene are admixed, whilst stirring, with ice and hydrochloric acid and diazotized in the usual manner. The resultant diazo solution is introduced, in the presence of excess sodium acetate, into an aqueous solution of 26.7 kg. 1-(4-su1phophenyl)-3-methyl-5-pyrazolone. The dyestuff thus obtained is precipitated with potassium chloride, filtered off and dried. It forms a yellow water-soluble powder and yields, when applied on cotton as indicated in Example 1 or according to the padding process or to the cold pad batch dyeing method, yellow dyeings of a very good fastness to light and wet processing. The fixation is very good.
The before-mentioned dyestuffs may also be prepared by starting from the monoazo dyestulfs obtained by combining the diazo compounds of 3-nitro-1-aminobenzene or 3-acetylamino-l-aminobenzene with 1-(4-sulfophenyl)- 3-methyl-5-pyrazolone, by converting these monoazo dyestuffs by reduction or saponification into the aminoazo dyestulf and by acylating the latter in the presence of sodium bicarbonate with the chloride or anhydride of the IS-methylsulfonyl-propionic acid.
A dyestulf of similar properties, but of a more greenish The following table enumerates some further dyestufis which may be obtained according to the process of the present invention:
Dlazo component Coupling component Shade 3-methyl-5-pyrazolone Greenish yellow.
NH.O0.0H1.0Hfl-SO1OH$ a 0 Redd ls]: yellow.
NH.CO.CHz.CHg.SOz.CH3
| NH.CO.CH2.CH .SO .CH3
NH.CO.CH .CH2.SO .CH
I NH.OO.CHz.CH2.SOz.CHa
Nmooemomsomom 1 (2,5 diehloro 4' sulfophenyl) B-methylfi-pyrazolone.
1 (2 sulfophenyl) 3 phenyl 5 pytazolone.
1-(3-su1iophenyl)-3-methyl-5pyrazolone 5-pyrazolone-3-carboxyli e acid 1 (4 sulfophenyl) 5 pyrazolone Q 3 carboxylic acid ethyl ester.
1 (4 sulfophenyl) 5 pyrazol ene 3 carboxyhc acld.
Greenlsh yellow.
Reddlsh yellow.
Dlazo component Coupling component Shade SlOaH ONES SOaH ONE:
NH.C0.0Hz.CHz.SOz-
NH.CO.CHI.CH2.SO1CH3 NH.CO.CHz.CHg.SOzCH S0311 ONE:
NH.CO.CH:.CH:.SO3CH| SOaH nmcosmomoQ SOQH l ONE;
ONE:
l mmooomcmsQ 1-pl1enyl-5-pyrazolon-3-corboxyllc acid 5-pyraz01one 3-carboxylic acid 5-pyrazolone-3-carboxylic acid amide 3-methyl-5-pyrazolone I-phenyI-S-met hYI-E: pyrazolone 1- (3-chlorophenyl)-3-metliyl-5-pyrazolone.
3-methyl-l'z-pyrazolonm Yellow.
Reddish yellow.
Yellow.
Reddish yellow.
GreeniSh yellow.
Diazo component Coupling component Shad S 03H ONE; 3-methyl-5-pyrazo1one Gteenish yellow.
1 NELC O .CHz. CH2.S. C H
SlO H ONH2 do Do.
I NH. O 0. CH2. CH2.SO. 02H;
SlO H O-NHQ do Reddish yellow. NH.SOz. CH2. cmso-O NH: 1-(4-su1fopheny1)-3-methy1-5-prazo1one Yellow.
CH3 N C O.CH2.CHz.SO2. CzH5 NH, do I Greem'sh yellow.
0 O OH- I IH. 0 0.0112. CHa.SO2-
(I3 0 OH NH: do Do.
1110 0.0112. CH2.SO1O
-NH d0 D0.
01 1 IH.C O CH2. 0112.802. OH;
NH, .r1n Do.
I NELC O. CHmCHmSOnCHz NH: Yellow.
Diazo component Coupling component Shade 1(4-su1fophenyl)-pyrazolone-3-carboxylic acid. Reddish yellow.
l CH1. CH1 NC\ /CH2 CH2. CH:
0 ocmomsmQ IIIH:
. do D0.
G O CHzCHzSOaCHa w do .t Do.
. F O N C 0 CH2. CH2.SO2. CH
. d0 Yellow.
NH.CO.CHaCH2.SOz.CHr-C in which Y is a radical selected from the group consisting of ethylene and vinylene,
Z is a bivalent radical selected from the group consisting of S0 SO, and S,
R is a radical selected from the group consisting of lower alkyl, phenyl, and benzyl,
R" is a substituent selected from the group consisting of OH and H2,
45 R' is a substituent selected from the group consisting of hydrogen and phenyl,
R"" is a radical selected from the group consisting of methyl, phenyl, carboxyl, carbamido, and lower carbalkoxy,
50 n is an integer consisting of 0 and 1.
References Cited by the Examiner UNITED STATES PATENTS 1,594,867 8/26 Zitscher 260-162 X FOREIGN PATENTS 520,239 3/31 Germany.
CHARLES B. PARKER, Primary Examiner.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC0026101 | 1962-01-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3215686A true US3215686A (en) | 1965-11-02 |
Family
ID=7018031
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US252605A Expired - Lifetime US3215686A (en) | 1962-01-27 | 1963-01-21 | Monoazo dyestuffs |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3215686A (en) |
| CH (1) | CH432682A (en) |
| DE (1) | DE1444588A1 (en) |
| GB (1) | GB973786A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2169085A1 (en) * | 1972-01-27 | 1973-09-07 | Ciba Geigy Ag | |
| US3853840A (en) * | 1965-12-08 | 1974-12-10 | Bayer Ag | Reactive dyestuffs containing a fiber-reactive alkylsulphonylpyrimidyl group |
| US4210582A (en) * | 1972-01-27 | 1980-07-01 | Ciba-Geigy Corporation | Water-soluble pyrazolone-imide containing azo dyestuffs |
| US6281339B1 (en) * | 1999-09-16 | 2001-08-28 | Ciba Specialty Chemicals Corporation | Addition products of acryloylamino-substituted dyes, and the preparation and use thereof |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2935681A1 (en) * | 1979-09-04 | 1981-03-12 | Bayer Ag, 5090 Leverkusen | REACTIVE DYES |
| DE3023855A1 (en) * | 1980-06-25 | 1982-01-14 | Bayer Ag, 5090 Leverkusen | REACTIVE DYES, METHOD FOR THEIR PRODUCTION AND THEIR USE FOR COLORING AND PRINTING FIBER MATERIALS CONTAINING HYDROXYL GROUPS OR NITROGEN MATERIALS |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1594867A (en) * | 1923-05-03 | 1926-08-03 | Ig Farbenindustrie Ag | Monoacylacetyl bodies containing azo or azoxy groups and process of making same |
| DE520239C (en) * | 1927-07-15 | 1931-03-16 | I G Farbenindustrie Akt Ges | Process for the preparation of azo dyes |
-
1962
- 1962-01-27 DE DE19621444588 patent/DE1444588A1/en active Pending
-
1963
- 1963-01-21 US US252605A patent/US3215686A/en not_active Expired - Lifetime
- 1963-01-25 CH CH93863A patent/CH432682A/en unknown
- 1963-01-25 GB GB3217/63A patent/GB973786A/en not_active Expired
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1594867A (en) * | 1923-05-03 | 1926-08-03 | Ig Farbenindustrie Ag | Monoacylacetyl bodies containing azo or azoxy groups and process of making same |
| DE520239C (en) * | 1927-07-15 | 1931-03-16 | I G Farbenindustrie Akt Ges | Process for the preparation of azo dyes |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3853840A (en) * | 1965-12-08 | 1974-12-10 | Bayer Ag | Reactive dyestuffs containing a fiber-reactive alkylsulphonylpyrimidyl group |
| FR2169085A1 (en) * | 1972-01-27 | 1973-09-07 | Ciba Geigy Ag | |
| US4210582A (en) * | 1972-01-27 | 1980-07-01 | Ciba-Geigy Corporation | Water-soluble pyrazolone-imide containing azo dyestuffs |
| US6281339B1 (en) * | 1999-09-16 | 2001-08-28 | Ciba Specialty Chemicals Corporation | Addition products of acryloylamino-substituted dyes, and the preparation and use thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| GB973786A (en) | 1964-10-28 |
| DE1444588A1 (en) | 1968-11-21 |
| CH432682A (en) | 1967-03-31 |
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